HCID 20333315, compound → HCID 86612032, compound

HRID 2074466Notes

Reaction equation

HRID 2074466 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([C:10]2[CH:15]=[C:14]([O:16][CH3:17])[C:13]([O:18][CH3:19])=[C:12]([O:20][CH3:21])[CH:11]=2)[O:5][C:6]=1[CH2:7][CH2:8][OH:9].[C:22]1([CH3:32])[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1.N1C=CC=CC=1>O>[C:22]1([CH3:32])[CH:27]=[CH:26][C:25]([S:28]([O:9][CH2:8][CH2:7][C:6]2[O:5][C:4]([C:10]3[CH:15]=[C:14]([O:16][CH3:17])[C:13]([O:18][CH3:19])=[C:12]([O:20][CH3:21])[CH:11]=3)=[N:3][C:2]=2[CH3:1])(=[O:30])=[O:29])=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 20333315HCID 20333315, compoundHCID 67089493HCID 67089493, compound

Product 1

HCID 86612032HCID 86612032, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To the solution of 2-[4-methyl-2-(3,4,5-trimethoxyphenyl)-1,3-oxazol-5-yl]ethanol (2.93 g, 10 mmol) in 30 ml of pyridine 4-toluenesulfonyl chloride (1.9 g, 10 mmol) was added portionwise at room temperature. Subsequently, the reaction mixture was stirred for 5 h at room temperature, and then poured into 200 ml of water and extracted (3×) with 50 ml of dichloromethane. The combined extracts were washed with 1M HCl, an aqueous solution of sodium bicarbonate, and brine. The organic phase was dried over magnesium sulfate and the solvent was evaporated, to obtain a product, 2-[4-methyl-2-(3,4,5-trimethoxyphenyl)-1,3-oxazol-5-yl]ethyl 4-toluenesulfonate having the purity of ca. 95%.

Workup

  1. extractionextracted (3×) with 50 ml of dichloromethane
  2. washThe combined extracts were washed with 1M HCl
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-95518a8bf4ad4998a86e84fd4a06e074
Source dataset
uspto-grants-2011_04
Patent number
US07919515B2

Reaction notes

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